Agricultural fungicidal method

ABSTRACT

Agricultural fungicidal compositions containing as an active ingredient one or more 4-aminoquinazoline derivatives. The amino group is substituted, e.g., with a phenoxyalkylene, and the quinazoline nucleus may be substituted at 2- and or 6-positions.

The invention relates to agricultural fungicidal compositions containingas an active ingredient one or more 4-aminoquinazoline derivatives.

More particularly, it relates to agricultural fungicidal compositionscontaining as an active ingredient one or more 4-aminoquinazolinederivatives represented by formula (I): ##STR1## in which:

A and B are the same or different and each represents a hydrogen atom, alower alkyl group, a halogen atom or a nitro group;

X represents an alkylene group;

Y represents an oxygen atom or a sulfur atom;

Z represents an alkyl group, an aralkyl group;

a naphthyl group, an unsubstituted phenyl group or a phenyl groupsubstituted with 1 to 3 substituents which are the same or different andare selected from the group consisting of a lower alkyl group, an alkoxygroup, an alkylthio group, a phenyl group, a trifluoromethyl group and ahalogen atom; or salts thereof.

A class of 4-aminoquinazoline derivatives is disclosed in JapanesePatent Publication Specification No. 43-29033, which corresponds to U.S.Pat. No. 3,541,094 as being effective controlling agents againstphytopathogenic fungi.

The inventors have found that the compounds of formula (I) show a broadand superior fungicidal activity than the known compounds mentionedabove against bacteria and fungi parasitic on agricultural andhorticultural plants. More specifically, the compounds of formula (I)show a remarkable controlling effect against, for example, blast, brownspot, sheath blight and bacterial leaf blight of rice plants; lateblight and early blight of tomatoes; and anthracnose, downy mildew andpowdery mildew of cucumbers. They also show a controlling effect againstphytoparasitic soil fungi, as well as algal fungi which adversely affectthe germination of rice plants.

Further, some of the compounds of formula (I) show a strong inhibitingactivity of ingestion against the fourth to final instar larvae ofLepidoptera such as cabbage armyworm and tobacco cutworm, and thereforeare useful as an insect repellent. Furthermore, some of the compounds offormula (I) may be used as an insecticidal and acaricidal agent gainst,e.g., two-spotted spider mite.

In the compounds of formula (I), when A and/or B each represents a loweralkyl group, it may be a straight or branched chain alkyl having 1 to 4carbon atoms, for example, a methyl, ethyl, n-propyl, isopropyl, n-butylor sec-butyl, preferably a methyl.

When A and/or B each represents a halogen atom, it may be, for example,a chlorine, bromine, fluorine or iodine, preferably a chlorine.

X is a straight or branched alkylene and it may be, for example, amethylene, ethylene, methylmethylene, trimethylene, ethylmethylene,dimethylmethylene, propylene, tetramethylene, 1,1-dimethylethylene,1,2-dimethylethylene, 2,2-dimethylethylene, 1-ethylethylene,2-ethylethylene, pentamethylene, hexamethylene, heptamethylene,octamethylene, 2-ethylhexamethylene, 5-ethylhexamethylene,decamethylene, dodecamethylene, hexadecamethylene or octadecamethylene;and it is preferably a straight or branched chain alkylene having 2 to 8carbon atoms.

When Z is an alkyl group, it may be, for example a methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl,isoamyl, sec-amyl, n-heptyl, n-octyl, 2-ethylhexyl, decyl, dodecyl,tetradecyl, hexadecyl or octadecyl; and it is preferably a straight orbranched alkyl having 1 to 8 carbon atoms.

When Z is a naphthyl group, it may be a 1-naphthyl or 2-naphthyl.

When Z is an aralkyl group, it may be, for example, a benzyl,α-methylbenzyl or phenethyl, preferably a benzyl.

When Z is a phenyl group substituted with lower alkyl, the lower alkylmay be straight or branched chain alkyl having 1 to 4 carbon atoms suchas methyl, ethyl, n-propyl isopropyl, n-butyl or sec-butyl, preferablymethyl.

When Z is a phenyl group substituted with lower alkoxy, the lower alkoxymay be straight or branched chain alkoxy having 1 to 4 carbon atoms suchas methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy or isobutoxy,preferably methoxy or ethoxy.

When Z is a phenyl group substituted with lower alkylthio, the loweralkylthio may be straight or branched chain alkylthio having 1 to 4carbon atoms such as methylthio, ethylthio, n-propylthio, isopropylthio,n-butylthio or isobutylthio, preferably methyl thio.

When Z is a phenyl group substituted with halogen atom, the halogen atommay be chlorine, bromine, fluorine or iodine, preferably chlorine.

Of the compounds of formula (I), the preferable class of compounds iswhen A is a hydrogen atom or a chlorine atom; B is a hydrogen atom, amethyl group, a chlorine atom or a nitro group; X is a straight orbranched alkylene group having from 2 to 8 carbon atoms; and Z is anunsubstituted phenyl group or a phenyl group substituted with 1 to 3substituents which are the same or different and are selected from thegroup consisting of a methyl, methoxy, ethoxy, methylthio,trifluoromethyl and chlorine.

Among the preferable compounds mentioned above, the more preferableclass of compounds is when both A and B are hydrogen atoms; X is astraight or branched chain alkylene group having 2 to 8 carbon atoms;and Z is an unsubstituted phenyl group or a phenyl group substitutedwith a methyl, methoxy, ethoxy or chlorine.

The most preferable class of compounds is when both A and B are hydrogenatoms; X is a straight or branched alkylene group having 2 to 8 carbonatoms; Y is an oxygen atom; and Z is an unsubstituted phenyl group or aphenyl group substituted with a methyl, methoxy, ethoxy or chlorine.

As can be understood by formula (I), the compounds of the invention haveat least one asymmetric carbon atom, depending on the species of thealkylene group X. In such cases, there can be present various differentoptical isomers. It is, therefore, to be understood that the individualstereoisomers as well as physical or racemic mixtures thereof areincluded within the scope of the invention.

The compounds of formula (I) may readily form acid addition salts; andsuch salts may also be used as the active ingredient of the agriculturalfungicides of the invention.

Acids to form addition salts include: inorganic acids such ashydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid andphosphoric acid; carboxylic acids such as formic acid, oxalic acid andtrichloroacetic acid; and organic sulfonic acids such as methanesulfonicacid, benzenesulfonic acid and toluenesulfonic acid. Thereof,hydrochloric acid is preferable.

Further, the compounds of formula (I) may form hydrates with water; andthe hydrates may also be used as the active ingredient of theagricultural fungicides of the invention.

The compounds of formula (I) used as the active ingredient of thefungicides of the invention will be illustrated below. The numbersappended to the compounds will be used to identify them hereafter.

1. 4-(2-Methoxyethyl)aminoquinazoline

2. 4-(2-Ethoxyethyl)aminoquinazoline

3. 4-(2-Ethylthioethyl)aminoquinazoline

4. 2-Chloro-4-(2-ethoxyethyl)aminoquinazoline

5. 2-Chloro-4-(2-ethylthioethyl)aminoquinazoline

6. 6-Chloro-4-(2-ethoxyethyl)aminoquinazoline

7. 4-(2-n-Propylthioethyl)aminoquinazoline

8. 4-(2-Phenoxyethyl)aminoquinazoline

9. 4-(2-Phenylthioethyl)aminoquinazoline

10. 2-Chloro-4-(2-phenoxyethyl)aminoquinazoline

11. 2-Chloro-4-(2-phenylthioethyl)aminoquinazoline

12. 6-Chloro-4-(2-phenoxyethyl)aminoquinazoline

13. 6-Methyl-4-(2-phenoxyethyl)aminoquinazoline

14. 4-[2-(2-Chlorophenoxy)ethyl]aminoquinazoline

15. 4-[2-(2-Bromophenoxy)ethyl]aminoquinazoline

16. 4-[2-(2-Iodophenoxy)ethyl]aminoquinazoline

17. 4-[2-(2-Fluorophenoxy)ethyl]aminoquinazoline

18. 2-Chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline

19. 6-Chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline

20. 4-[2-(2-Methylphenoxy)ethyl]aminoquinazoline

21. 4-[2-(2-Methylphenylthio)ethyl]aminoquinazoline

22. 2-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline

23. 6-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline

24. 6-Methyl-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline

25. 6-Isopropyl-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline

26. 2-Chloro-4-[2-(2-methylphenylthio)ethyl]aminoquinazoline

27. 4-[2-(2-Ethylphenoxy)ethyl]aminoquinazoline

28. 4-[2-(2-Isopropylphenoxy)ethyl]aminoquinazoline

29. 4-[2-(2-sec-Butylphenoxy)ethyl]aminoquinazoline

30. 4-[2-(2-Methoxyphenoxy)ethyl]aminoquinazoline

31. 6-Methyl-4-[2-(2-methoxyphenoxy)ethyl]aminoquinazoline

32. 4-[2-(2-Ethoxyphenoxy)ethyl]aminoquinazoline

33. 6-Chloro-4-[2-(2-ethoxyphenoxy)ethyl]aminoquinazoline

34. 4-[2-(2-n-Butoxyphenoxy)ethyl]aminoquinazoline

35. 4-[2-(o-Phenylphenoxy)ethyl]aminoquinazoline

36. 4-[2-(p-Phenylphenoxy)ethyl]aminoquinazoline

37. 6-Chloro-4-[2-(o-phenylphenoxy)ethyl]aminoquinazoline

38. 4-[2-(2-Trifluoromethylphenoxy)ethyl]aminoquinazoline

39. 4-[2-(3-Chlorophenoxy)ethyl]aminoquinazoline

40. 6-Methyl-4-[2-(3-chlorophenoxy)ethyl]aminoquinazoline

41. 4-[2-(3-Methylphenoxy)ethyl]aminoquinazoline

42. 4-[2-(3-Methylphenylthio)ethyl]aminoquinazoline

43. 2-Chloro-4-[2-(3-methylphenoxy)ethyl]aminoquinazoline

44. 2-Chloro-4-[2-(3-methylphenylthio)ethyl]aminoquinazoline

45. 4-[2-(3-Trifluoromethylphenoxy)ethyl]aminoquinazoline

46. 4-[2-(4-Chlorophenoxy)ethyl]aminoquinazoline

47. 4-[2-(4-Chlorophenylthio)ethyl]aminoquinazoline

48. 4-[2-(4-Bromophenoxy)ethyl]aminoquinazoline

49. 4-[2-(4-Bromophenylthio)ethyl]aminoquinazoline

50. 4-[2-(4-Fluorophenoxy)ethyl]aminoquinazoline

51. 4-[2-(4-Methylphenoxy)ethyl]aminoquinazoline

52. 4-[2-(4-Methylphenylthio)ethyl]aminoquinazoline

53. 2-Chloro-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline

54. 2-Chloro-4-[2-(4-Methylphenylthio)ethyl]aminoquinazoline

55. 6-Methyl-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline

56. 4-[2-(4-tert-Butylphenoxy)ethyl]aminoquinazoline

57. 4-[2-(4-Methoxyphenoxy)ethyl]aminoquinazoline

58. 4-[2-(4-Isopropoxyphenoxy)ethyl]aminoquinazoline

59. 4-[2-(2,4-Dichlorophenoxy)ethyl]aminoquinazoline

60. 4-[2-(2,4-Dibromophenoxy)ethyl]aminoquinazoline

61. 6-Chloro-4-[2-(2,4-dichlorophenoxy)ethyl]aminoquinazoline

62. 4-[2-(2-Methyl-4-chlorophenoxy)ethyl]aminoquinazoline

63. 2-Chloro-4-[2-(2-methyl-4-chlorophenoxy)ethyl]aminoquinazoline

64. 4-[2-(2,4-Dimethylphenoxy)ethyl]aminoquinazoline

65. 4-[2-(2-Chloro-4-methoxyphenoxy)ethyl]aminoquinazoline

66. 4-[2-(2-Bromo-4-isopropylphenoxy)ethyl]aminoquinazoline

67. 6-Chloro-4-[2-(2,5-dimethylphenoxy)ethyl]aminoquinazoline

68. 4-[2-(2,6-Dimethylphenoxy)ethyl]aminoquinazoline

69. 4-[2-(2,6-Diethylphenoxy)ethyl]aminoquinazoline

70. 2-Chloro-4-[2-(2,6-dimethylphenoxy)ethyl]aminoquinazoline

71. 4-[2-(3-Methyl-4-methylthiophenoxy)ethyl]aminoquinazoline

72. 6-Bromo-[2-(3-methyl-4-n-butylthiophenylthio)ethyl]aminoquinazoline

73. 4-[2-(3,5-Dimethylphenoxy)ethyl]aminoquinazoline

74. 2-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline

75. 6-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline

76. 4-[2-(2,4,5-Trichlorophenoxy)ethyl]aminoquinazoline

77. 4-[2-(2,4,6-Tribromophenoxy)ethyl]aminoquinazoline

78. 6-Chloro-4-[2-(2,4,5-trichlorophenoxy)ethyl]aminoquinazoline

79. 4-[2-(2,4,6-Trichlorophenoxy)ethyl]aminoquinazoline

80. 4-[2-(2,4,6-Triiodophenoxy)ethyl]aminoquinazoline

81. 6-Chloro-4-[2-(2,4,6-trichlorophenoxy)ethyl]aminoquinazoline

82. 4-[2-(2,3,6-Trimethylphenoxy)ethyl]aminoquinazoline

83. 6-Bromo-4-[2-(2,6-dichloro-4-bromophenoxy)ethyl]aminoquinazoline

84. 4-[2-(1-Naphthoxy)ethyl]aminoquinazoline

85. 6-Chloro-4-[2-(1-naphthoxy)ethyl]aminoquinazoline

86. 4-[2-(Benzyloxy)ethyl]aminoquinazoline

87. 4-[2-Benzylthio)ethyl]aminoquinazoline

88. 2-Chloro-4-[2-(benzylthio)ethyl]aminoquinazoline

89. 4-[2-(Phenethyloxy)ethyl]aminoquinazoline

90. 4-[2-(α-Methylbenzyloxy)ethyl]aminoquinazoline

91. 4-(3-Methoxypropyl)aminoquinazoline

92. 4-(3-Ethoxypropyl)aminoquinazoline

93. 2-Chloro-4-(3-ethoxypropyl)aminoquinazoline

94. 6-Nitro-4-(3-ethoxypropyl)aminoquinazoline

95. 4-(3-Isopropoxypropyl)aminoquinazoline

96. 4-(3-n-Butoxypropyl)aminoquinazoline

97. 2-Chloro-4-(3-n-butoxypropyl)aminoquinazoline

98. 4-[3-(2-Ethylhexyloxy)propyl]aminoquinazoline

99. 6-Nitro-4-[3-(2-ethylhexyloxy)propyl]aminoquinazoline

100. 4-(3-Dodecyloxypropyl)aminoquinazoline

101. 6-Iodo-4-(3-stearyloxypropyl)aminoquinazoline

102. 4-(3-Phenoxypropyl)aminoquinazoline

103. 4-(3-Phenylthiopropyl)aminoquinazoline

104. 2-Chloro-4-(3-phenoxypropyl)aminoquinazoline

105. 2-Chloro-4-(3-phenylthiopropyl)aminoquinazoline

106. 6-Methyl-4-(3-phenoxypropyl)aminoquinazoline

107. 6-Methyl-4-(3-phenylthiopropyl)aminoquinazoline

108. 6-Nitro-4-(3-phenoxypropyl)aminoquinazoline

109. 4-[3-(2-Chlorophenoxy)propyl]aminoquinazoline

110. 4-[3-(2-Methylphenoxy)propyl]aminoquinazoline

111. 4-[3-(2-Methylphenylthio)propyl]aminoquinazoline

112. 4-[3-(2-Methoxyphenoxy)propyl]aminoquinazoline

113. 4-[3-(3-Chlorophenoxy)propyl]aminoquinazoline

114. 4-[3-(3-Methylphenoxy)propyl]aminoquinazoline

115. 4-[3-(3-Methylphenylthio)propyl]aminoquinazoline

116. 2-Chloro-4-[3-(3-methylphenoxy)propyl]aminoquinazoline

117. 2-Chloro-4-[3-(3-methylphenylthio)propyl]aminoquinazoline

118. 4-[3-(4-Chlorophenoxy)propyl]aminoquinazoline

119. 2-Chloro-4-[3-(4-chlorophenoxy)propyl]aminoquinazoline

120. 4-[3-(4-Methylphenoxy)propyl]aminoquinazoline

121. 4-[3-(4-Methylphenylthio)propyl]aminoquinazoline

122. 2-Chloro-4-[3-(4-methylphenylthio)propyl]aminoquinazoline

123. 6-Iodo-4-[3-(4-tert-butylphenoxy)propyl]aminoquinazoline

124. 4-[3-(4-methoxyphenoxy)propyl]aminoquinazoline

125. 4-[3-(2,5-Dimethylphenoxy)propyl]aminoquinazoline

126. 4-[3-(2-Methyl-4-chlorophenoxy)propyl]aminoquinazoline

127. 4-[3-(2-Chloro-4-methoxyphenoxy)propyl]aminoquinazoline

128. 4-[3-(3-Methyl-4-chlorophenoxy)propyl]aminoquinazoline

129. 4-[3-(3,5-Dimethylphenoxy)propyl]aminoquinazoline

130. 6-Chloro-4-[3-(2,4,6-trimethylphenoxy)propyl]aminoquinazoline

131. 4-[3-(1-Naphthoxy)propyl]aminoquinazoline

132. 2-Chloro-4-[3-(2-naphthylthio)propyl]aminoquinazoline

133. 4-(1-Methyl-2-methoxyethyl)aminoquinazoline

134. 4-(1-Methyl-2-octyloxyethyl)aminoquinazoline

135. 4-(1-Methyl-2-phenoxyethyl)aminoquinazoline

136. 2-Chloro-4-(1-methyl-2-phenoxyethyl)aminoquinazoline

137. 6-Methyl-4-(1-methyl-2-phenoxyethyl)aminoquinazoline

138. 6-Bromo-4-(1-methyl-2-phenylthioethyl)aminoquinazoline

139. 4-[1-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

140. 4-[1-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline

141. 4-[1-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline

142. 4-[1-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

143. 4-[1-Methyl-2-(3-isopropylphenylthio)ethyl]aminoquinazoline

144. 4-[1-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

145. 2-Chloro-4-[1-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

146. 6-Bromo-4-[1-methyl-2-(4-iodophenylthio)ethyl]aminoquinazoline

147. 4-[1-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

148. 2-Chloro-4-[1-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

149. 4-[1-Methyl-2-(4-n-butoxyphenoxy)ethyl]aminoquinazoline

150. 4-[1-Methyl-2-(4-phenylphenoxy)ethyl]aminoquinazoline

151. 4-(2-Methyl-2-phenoxyethyl)aminoquinazoline

152. 2-Chloro-4-(2-methyl-2-phenoxyethyl)aminoquinazoline

153. 4-[2-Methyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline

154. 4-[2-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

155. 2-Chloro-4-[2-methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

156. 6-Chloro-4-[2-methyl-2-(2-tert-butylphenoxy)ethyl]aminoquinazoline

157. 4-[2-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline

158. 4-[2-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline

159. 4-[2-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

160. 4-[2-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

161. 4-[2-Methyl-2-(4-bromophenoxy)ethyl]aminoquinazoline

162. 2-Chloro-4-[2-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

163. 4-[2-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

164. 2-Chloro-4-[2-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

165. 4-[2-Methyl-2-(4-phenylphenoxy)ethyl]aminoquinazoline

166. 6-Methyl-4-[2-methyl-2-(4-n-butylthiophenoxy)ethyl]aminoquinazoline

167. 4-(4-Ethoxybutyl)aminoquinazoline

168. 4-(4-Dodecylthiobutyl)aminoquinazoline

169. 4-(4-Benzyloxybutyl)aminoquinazoline

170. 4-(4-Phenoxybutyl)aminoquinazoline

171. 6-Methyl-4-(4-phenoxybutyl)aminoquinazoline

172. 4-[4-(2-Chlorophenoxy)butyl]aminoquinazoline

173. 4-[4-(2-Methylphenoxy)butyl]aminoquinazoline

174. 4-[4-(2-Methoxyphenoxy)butyl]aminoquinazoline

175. 4-[4-(3-Methylphenoxy)butyl]aminoquinazoline

176. 4-[4-(3-Chlorophenoxy)butyl]aminoquinazoline

177. 6-Bromo-4-[4-(3-bromophenylthio)butyl]aminoquinazoline

178. 4-[4-(3-Phenylphenoxy)butyl]aminoquinazoline

179. 4-[4-(4-Methylphenoxy)butyl]aminoquinazoline

180. 4-[4-(4-Isopropylphenoxy)butyl]aminoquinazoline

181. 4-[4-(4-Methylthiophenylthio)butyl]aminoquinazoline

182. 4-(2-Ethyl-2-benzyloxyethyl)aminoquinazoline

183. 4-(2-Ethyl-2-phenoxyethyl)aminoquinazoline

184. 4-[2-Ethyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline

185. 2-Chloro-4-[2-ethyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

186. 4-(1-Ethyl-2-methoxyethyl)aminoquinazoline

187. 6-Bromo-4-(1-ethyl-2-benzyloxyethyl)aminoquinazoline

188. 2-Chloro-4-(1-ethyl-2-phenoxyethyl)aminoquinazoline

189. 4-[1-Ethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline

190. 4-[1-Ethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

191. 4-[1-Ethyl-2-(4-isopropoxyphenylthio)ethyl]aminoquinazoline

192. 4-(2,2-Dimethyl-2-ethoxyethyl)aminoquinazoline

193. 2-Chloro-4-(2,2-dimethyl-2-octyloxyethyl)aminoquinazoline

194. 6-Methyl-4-(2,2-dimethyl-2-benzylthioethyl)aminoquinazoline

195. 4-(2,2-Dimethyl-2-phenoxyethyl)aminoquinazoline

196. 2-Chloro-4-(2,2-dimethyl-2-phenoxyethyl)aminoquinazoline

197. 4-[2,2-Dimethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline

198. 4-[2,2-Dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

199. 2-Chloro-4-[2,2-dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

200. 4-[2,2-Dimethyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline

201. 4-[2,2-Dimethyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline

202. 4-[2,2-Dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

203. 2-Chloro-4-[2,2-dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

204. 4-[2,2-Dimethyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

205. 4-[2,2-Dimethyl-2-(4-bromophenoxy)ethyl]aminoquinazoline

206. 4-[2,2-Dimethyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

207. 4-[2,2-Dimethyl-2-(4-isopropylphenylthio)ethyl]aminoquinazoline

208. 2-Chloro-4-[2,2-dimethyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

209. 4-(1,1-Dimethyl-2-phenoxyethyl)aminoquinazoline

210. 4-[1,1-Dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

211. 4-[1,1-Dimethyl-2-(3-methoxyphenoxy)ethyl]aminoquinazoline

212. 4-(1,2-Dimethyl-2-dodecyloxyethyl)aminoquinazoline

213. 4-(1,2-Dimethyl-2-phenoxyethyl)aminoquinazoline

214. 4-[1,2-Dimethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline

215. 4-[1,2-Dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

216.2-Chloro-4-[1,2-dimethyl-2-(4-methoxyphenylthio)ethyl]aminoquinazoline

217. 4-(5-n-Butoxypentyl)aminoquinazoline

218. 4-(5-Octoxypentyl)aminoquinazoline

219. 4-[5-(2-Ethylhexyloxy)pentyl]aminoquinazoline

220. 4-(5-Stearyloxypentyl)aminoquinazoline

221. 4-(5-Benzylthiopentyl)aminoquinazoline

222. 4-(5-Phenoxypentyl)aminoquinazoline

223. 4-[5-(2-Chlorophenoxy)pentyl]aminoquinazoline

224. 2-Chloro-4-[5-(2-chlorophenoxy)pentyl]aminoquinazoline

225. 4-[5-(2-Methylphenoxy)pentyl]aminoquinazoline

226. 4-[5-(2-Methoxyphenoxy)pentyl]aminoquinazoline

227. 2-Chloro-4-[5-(2-methoxyphenylthio)pentyl]aminoquinazoline

228. 4-[5-(3-Chlorophenoxy)pentyl]aminoquinazoline

229. 4-[5-(3-Methylphenoxy)pentyl]aminoquinazoline

230. 4-[5-(3-Methoxyphenoxy)pentyl]aminoquinazoline

231. 4-[5-(4-Chlorophenoxy)pentyl]aminoquinazoline

232. 4-[5-(4-Methylphenoxy)pentyl]aminoquinazoline

233. 4-[5-(4-Methoxyphenoxy)pentyl]aminoquinazoline

234. 4-(6-Phenoxyhexyl)aminoquinazoline

235. 4-[6-(2-Chlorophenoxy)hexyl]aminoquinazoline

236. 4-[6-(2-Methylphenoxy)hexyl]aminoquinazoline

237. 6-Chloro-4-[6-(2-methylphenoxy)hexyl]aminoquinazoline

238. 4-[6-(3-Chlorophenoxy)hexyl]aminoquinazoline

239. 4-[6-(3-Methylphenoxy)hexyl]aminoquinazoline

240. 4-[6-(3-Methoxyphenoxy)hexyl]aminoquinazoline

241. 4-[6-(4-Chlorophenoxy)hexyl]aminoquinazoline

242. 4-[6-(4-Chlorophenylthio)hexyl]aminoquinazoline

243. 4-[6-(4-Methylphenoxy)hexyl]aminoquinazoline

244. 4-[6-(4-Methoxyphenoxy)hexyl]aminoquinazoline

245. 2-Chloro-4-[6-(4-methoxyphenoxy)hexyl]aminoquinazoline

246. 4-(7-Isopropoxyheptyl)aminoquinazoline

247. 4-(7-Dodecylthioheptyl)aminoquinazoline

248. 4-(7-Phenoxyheptyl)aminoquinazoline

249. 4-[7-(2-Chlorophenoxy)heptyl]aminoquinazoline

250. 4-[7-(2-Methylphenoxy)heptyl]aminoquinazoline

251. 4-[7-(2-Methoxyphenoxy)heptyl]aminoquinazoline

252. 4-[7-(3-Chlorophenoxy)heptyl]aminoquinazoline

253. 4-[7-(3-Methylphenoxy)heptyl]aminoquinazoline

254. 4-[7-(4-Chlorophenoxy)heptyl]aminoquinazoline

255. 4-[7-(4-Methylphenoxy)heptyl]aminoquinazoline

256. 4-[7-(4-Methoxyphenoxy)heptyl]aminoquinazoline

257. 4-[7-(2,4-Dichlorophenoxy)heptyl]aminoquinazoline

258. 4-[7-(3,5-Dimethylphenoxy)heptyl]aminoquinazoline

259. 4-(8-Methoxyoctyl)aminoquinazoline

260. 4-(8-Benzylthiooctyl)aminoquinazoline

261. 4-(8-Phenoxyoctyl)aminoquinazoline

262. 4-[8-(2-Chlorophenoxy)octyl]aminoquinazoline

263. 4-[8-(2-Methylphenoxy)octyl]aminoquinazoline

264. 4-[8-(2-Methoxyphenoxy)octyl]aminoquinazoline

265. 4-[8-(3-Chlorophenoxy)octyl]aminoquinazoline

266. 4-[8-(3-Methylphenyl)octyl]aminoquinazoline

267. 4-[8-(3-Methoxyphenyl)octyl]aminoquinazoline

268. 4-[8-(4-Chlorophenoxy)octyl]aminoquinazoline

269. 4-[8-(4-Methylphenoxy)octyl]aminoquinazoline

270. 4-[8-(4-Methylthiophenoxy)octyl]aminoquinazoline

271. 4-[8-(4-Methoxyphenoxy)octyl]aminoquinazoline

272. 4-[8-(3,5-Dichlorophenoxy)octyl]aminoquinazoline

273. 4-[8-(2,6-Dimethylphenoxy)octyl]aminoquinazoline

274. 4-(10-Methoxydecyl)aminoquinazoline

275. 4-(10-Phenoxydecyl)aminoquinazoline

276. 4-[10-(2-Chlorophenoxy)decyl]aminoquinazoline

277. 4-[10-(3-Methylphenoxy)decyl]aminoquinazoline

278. 4-[10-(4-Methoxyphenoxy)decyl]aminoquinazoline

279. 4-(12-Phenoxydodecyl)aminoquinazoline

280. 4-[12-(2-Methylphenoxy)dodecyl]aminoquinazoline

281. 4-[12-(3-Chlorophenoxy)dodecyl]aminoquinazoline

282. 4-[12-(4-Methoxyphenoxy)dodecyl]aminoquinazoline

283. 4-(16-Phenoxyhexadecyl)aminoquinazoline

284. 4-(18-Phenoxyoctadecyl)aminoquinazoline

285. 4-[2-(2-n-Propylphenoxy)ethyl]aminoquinazoline

286. 6-Methyl-4-[4-(2-chlorophenoxy)butyl]aminoquinazoline

287. 4-[2-(2-Methoxy-4-methylphenoxy)ethyl]aminoquinazoline

288. 4-[2-(3-Methoxyphenoxy)ethyl]aminoquinazoline

289. 4-[2-(2-Methoxy-4-chlorophenoxy)ethyl]aminoquinazoline

290. 4-[2-(2-Methyl-3-chlorophenoxy)ethyl]aminoquinazoline

291. 2-Methyl-4-(3-phenoxypropyl)aminoquinazoline

292. 4-[2-(2,5-Dimethoxyphenoxy)ethyl]aminoquinazoline

293. 4-[2-(3,5-Dimethyl-4-bromophenoxy)ethyl]aminoquinazoline

294. 4-[2-(2,4-Dichloro-6-methylphenoxy)ethyl]aminoquinazoline

295. 4-[2-(2-Trifluoromethyl-4-chlorophenoxy)ethyl]aminoquinazoline

296. 4-[2-(2-n-Butylphenoxy)ethyl]aminoquinazoline

297. 4-[2-(2-tert-Butylphenoxy)ethyl]aminoquinazoline

The compounds of formula (I) may readily be prepared, for example, bythe following methods which can be performed under per se knownconditions: ##STR2## (In the above formulae, A, B, X, Y and Z are asdefined above).

The reaction is preferably carried out in the presence of a solvent anda base.

The nature of the solvent is not critical, provided that it has noadverse effect upon the reaction. Examples of suitable solvents include:Chlorinated or non-chlorinated aromatic, aliphatic or alicyclichydrocarbons, such as benzene, toluene, xylene, methylnaphthalene,petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene,methylene chloride, chloroform, dichloroethane, trichloroethylene andcyclohexane; ethers, such as diethyl ether, ethylene glycol dimethylether, tetrahydrofuran and dioxane; ketones, such as acetone and methylethyl ketone; alcohols, such as methanol, ethanol and ethylene glycol aswell as mixtures thereof with water; and mixtures of the above-mentionedsolvents.

Examples of bases include: organic bases, such as triethylamine,pyridine and N,N-diethylaniline; inorganic bases such as sodiumhydroxide, potassium hydroxide, sodium carbonate and potassiumcarbonate.

The reaction temperature is not critical and it ranges usually fromambient to a temperature at which the solvent used refluxes. It ispreferable that the reaction is performed with heating in order toshorten the reaction period.

After completion of the reaction, the desired compound may optionally bepurified by conventional methods such as recrystallization orchromatography.

Acid addition salts may readily be prepared by introducing an acid intothe reaction mixture and then by evaporating the solvent.

Similarly, hydrates may usually be obtained by recrystallizing thedesired compound from a solvent containing water.

Preparation of the active ingredient compound of the invention isillustrated by the following Examples:

Preparation 1. Compound No. 19

To a solution of 2.0 g (0.01 mol) of 4,6-dichloroquinazoline in 50 ml ofbenzene were added 1.0 g (0.01 mol) of triethylamine and 1.7 g (0.01mol) of 2-(2-chlorophenoxy) ethylamine, and the mixture was refluxed,with stirring, for 3 hours.

After completion of the reaction, the benzene was removed from thereaction mixture by evaporation under reduced pressure, and the crystalswhich were separated were washed with water and collected by filtration.Recrystallization of the crystals from ethanol gave 2.7 g of6-chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline in the form ofcolorless plates.

m.p. 176°˜178° C.

Elementary analysis (%): Calcd: C, 57.62; H, 3.78; N, 12.69. Found: C,57.50; H, 3.92; N, 12.57.

Preparation 2. Compound No. 31

To a solution of 1.8 g (0.01 mol) of 4-chloro-6-methylquinazoline in 50ml of benzene were added 1.0 g (0.01 mol) of triethylamine and 1.7 g(0.01 mol) of 2-(O-methoxyphenoxy)ethylamine, and the mixture washeated, with stirring, at 60°˜70° C. for 5 hours. After completion ofthe reaction, the benzene was evaporated under reduced pressure and theresidue was dissolved in chloroform, washed with water and dried overanhydrous sodium sulfate. The chloroform was evaporated under reducedpressure to leave crystals, which were recrystallized from ethanol,giving 0.9 g of 6-methyl-4-[2-(2-methoxyphenoxy)ethyl]-aminoquinazolinein the form of colorless plates.

m.p. 167°˜169° C.

Elementary analysis (%): Calcd: C, 69.88; H, 6.19; N, 13.58 Found: C,69.86; H, 6.15; N, 13.60

Preparation 3. Compound No. 49

To a solution of 2.5 g (0.015 mol) of 4-chloroquinazoline in 50 ml ofbenzene were added 1.5 g (0.015 mol) of triethylamine and 3.5 g (0.015mol) of 2-(p-bromophenylthio) ethylamine, and the mixture was heated,with stirring, at 70°˜80° C. for 3 hours. After completion of thereaction, the benzene was evaporated under reduced pressure and theresulting crystals were washed with water, collected by filtration andrecrystallized from ethanol, giving 3.0 g of4-[2-(4-bromophenylthio)ethyl]aminoquinazoline in the form of colorlessgranules.

m.p. 161°˜163° C.

Elementary analysis (%): Calcd: C, 52.95; H, 3.85; N, 11.41. Found: C,53.34; H, 3.92; N, 11.66.

Preparation 4. Compound No. 86

To a solution of 3.3 g (0.02 mol) of 4-chloroquinazoline in 50 ml ofbenzene were added 2.0 g (0.02 mol) of triethylamine and 3.0 g (0.02mol) of 2-benzyloxyethylamine, and the mixture was heated, withstirring, at 60°˜70° C. for 5 hours. After completion of the reaction,the benzene was evaporated under reduced pressure, and the resultingcrystals were washed with water, collected by filtration, dried andrecrystallized from benzene/n-hexane, affording 3.7 g of4-[2-(benzyloxy)ethyl]aminoquinazoline in the form of colorless needles.

m.p. 111°˜113° C.

Elementary analysis (%): Calcd: C, 73.09; H, 6.14; N, 15.04. Found: C,72.98; H, 6.11; N, 14.69.

Preparation 5. Compound No. 102

To a solution of 2.5 g (0.015 mol) of 4-chloroquinazoline in 50 ml ofbenzene were added 1.5 g (0.015 mol) of triethylamine and 2.3 g (0.015mol) of 3-phenoxypropylamine, and the mixture was refluxed for 3 hours.

After completion of the reaction, the benzene was evaporated underreduced pressure and the residue was washed with water, collected byfiltration to give crystals. The crystals were recrystallized from 70%ethanol, giving 1.5 g of 4-(3-phenoxypropyl)aminoquinazoline in the formof colorless flakes.

m.p. 129°˜131° C.

Elementary analysis (%): Calcd: C, 73.09; H. 6.14; N, 15.04. Found: C,72.69; H, 6.24; N, 14.66.

Preparation 6. Compound No. 108

To a solution of 1.7 g (0.008 mol) of 4-chloro-5-nitroquinazoline in 50ml of benzene were added 0.8 g (0.008 mol) of triethylamine and 1.2 g(0.008 mol) of 3-phenoxypropylamine, and the mixture was refluxed for 3hours on an oil bath. After cooling, crystals separated were collectedby filtration, washed with water and recrystallized from aqueousethanol, affording 6-nitro-4-(3-phenoxypropyl)aminoquinazoline as themonohydrate in the form of yellow needles.

m.p. 121°˜123° C.

Elementary analysis (%): Calcd: C, 60.38; H, 5.19; N, 16.44. Found: C,59.65; H, 5.26; N, 16.37.

Preparation 7. Compound No. 208

To a solution of 2.0 g (0.01 mol) of 2,4-dichloroquinazoline in 50 ml ofbenzene were added 1.0 g (0.01 mol) of triethylamine and 1.8 g (0.01mol) of 2,2-dimethyl-2-(4-methylphenoxy)-ethylamine and the mixture wasstirred at an ambient temperature for 4 hours. After completion of thereaction, the benzene was evaporated under reduced pressure, and theresidue was dissolved in chloroform, washed with water and dried overanhydrous sodium sulfate. The chloroform was removed by evaporationunder reduced pressure to leave crystals, which were recrystallized frombenzene/hexane, affording 2.3 g of2-chloro-4-[2,2-dimethyl-2-(4-methylphenoxy)ethyl]-aminoquinazoline inthe form of a colorless fine powder.

m.p. 121°˜124° C.

Elementary analysis (%): Calcd: C, 66.76; H, 5.90; N, 12.29. Found: C,66.52; H, 6.04; N, 11.93.

Preparation 8. Compound No. 222

To a solution of 1.7 g (0.01 mol) of 4-chloroquinazoline in 50 ml ofbenzene were added 1.0 g (0.01 mol) of triethylamine and 1.8 g (0.01mol) of 5-phenoxypentylamine, and the mixture was refluxed for 3 hours.After completion of the reaction, the benzene was evaporated underreduced pressure to leave crystals, which were washed with water,collected by filtration and recrystallized from aqueous ethanol, giving0.6 g of 4-(5-phenoxypentyl)aminoquinazoline in the form of colorlessflakes.

m.p. 106°˜108° C.

Elementary analysis (%): Calcd: C, 74.26; H, 6.84; N, 13.68. Found: C,74.95; H, 6.89; N, 13.75.

2.5 g of the 4-(5-phenoxypentyl)aminoquinazoline obtained according tothe process were dissolved in 100 ml of ethanol, and 2 g of 36%hydrochloric acid were added. The ethanol was removed by evaporationunder reduced pressure and the resulting residue was dried,recrystallized from aqueous ethanol, giving4-(5-phenoxypentyl)aminoquinazoline in the form of the hydrochloridemelting at 183°˜186° C.

Following the methods described in Preparations 1 to 8, the followingcompounds were obtained:

4-(2-Methoxyethyl)aminoquinazoline

m.p. 127°˜128° C.

4-(2-Ethoxyethyl)aminoquinazoline

m.p. 112°˜113° C.

4-(2-Ethylthioethyl)aminoquinazoline

m.p. 116°˜118° C.

2-Chloro-4-(2-ethoxyethyl)aminoquinazoline

m.p. 93°˜95° C.

2-Chloro-4-(2-ethylthioethyl)aminoquinazoline

m.p. 119°˜121° C.

6-Chloro-4-(2-ethoxyethyl)aminoquinazoline

m.p. 125°˜127° C.

4-(2-n-Propylthioethyl)aminoquinazoline

m.p. 95°˜98° C.

4-(2-Phenoxyethyl)aminoquinazoline

m.p. 183°˜185° C.

4-(2-Phenylthioethyl)aminoquinazoline

m.p. 137°˜139° C.

2-Chloro-4-(2-phenoxyethyl)aminoquinazoline

m.p. 172°˜174° C.

2-Chloro-4-(2-phenylthioethyl)aminoquinazoline

m.p. 210°˜212° C.

6-Chloro-4-(2-phenoxyethyl)aminoquinazoline

m.p. 155°˜158° C.

6-Methyl-4-(2-phenoxyethyl)aminoquinazoline

m.p. 138°˜140° C.

4-[2-(2-Chlorophenoxy)ethyl]aminoquinazoline

m.p. 161°˜163° C.

4-[2-(2-Bromophenoxy)ethyl]aminoquinazoline

m.p. 164°˜166° C.

4-[2-(2-Iodophenoxy)ethyl]aminoquinazoline

m.p. 161°˜163° C.

4-[2-(2-Fluorophenoxy)ethyl]aminoquinazoline

m.p. 164°˜166° C.

2-Chloro-4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline

m.p. 169°˜171° C.

4-[2-(2-Methoxyphenoxy)ethyl]aminoquinazoline

m.p. 138°˜140° C.

4-[2-(2-Methylphenylthio)ethyl]aminoquinazoline

m.p. 149°˜151° C.

2-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 176°˜178° C.

6-Chloro-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 168°˜171° C.

6-Methyl-4-[2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 161°˜164° C.

2-Chloro-4-[2-(2-methylphenylthio)ethyl]aminoquinazoline

m.p. 194°˜196° C.

4-[2-(2-Ethylphenoxy)ethyl]aminoquinazoline

m.p. 134°˜135° C.

4-[2-(2-Isopropylphenoxy)ethyl]aminoquinazoline

m.p. 132°˜134° C.

4-[2-(2-sec-Butylphenoxy)ethyl]aminoquinazoline

m.p. 128°˜130° C.

4-[2-(2-Methoxyphenoxy)ethyl]aminoquinazoline

m.p. 148°˜152° C.

4-[2-(2-Ethoxyphenoxy)ethyl]aminoquinazoline.monohydrate

m.p. 111°˜113° C.

6-Chloro-4-[2-(2-ethoxyphenoxy)ethyl]aminoquinazoline.monohydrate

m.p. 154°˜156° C.

4-[2-(2-Phenylphenoxy)ethyl]aminoquinazoline

m.p. 137°˜140° C.

4-[2-(3-Chlorophenoxy)ethyl]aminoquinazoline

m.p. 193°˜195° C.

6-Methyl-4-[2-(3-chlorophenoxy)ethyl]aminoquinazoline

m.p. 150°˜152° C.

4-[2-(3-Methylphenoxy)ethyl]aminoquinazoline

m.p. 184°˜186° C.

4-[2-(3-Methylphenylthio)ethyl]aminoquinazoline

m.p. 131°˜133° C.

2-Chloro-4-[2-(3-methylphenoxy)ethyl]aminoquinazoline

m.p. 162°˜164° C.

2-Chloro-4-[2-(3-methylphenylthio)ethyl]aminoquinazoline

m.p. 154°˜156° C.

4-[2-(3-Trifluoromethylphenoxy)ethyl]aminoquinazoline

m.p. 161°˜163° C.

4-[2-(4-Chlorophenoxy)ethyl]aminoquinazoline

m.p. 191°˜193° C.

4-[2-(4-Chlorophenylthio)ethyl]aminoquinazoline

m.p. 147°˜149° C.

4-[2-(4-Bromophenoxy)ethyl]aminoquinazoline

m.p. 161°˜163° C.

4-[2-(4-Fluorophenoxy)ethyl]aminoquinazoline

m.p. 189°˜190° C.

4-[2-(4-Methylphenoxy)ethyl]aminoquinazoline

m.p. 153°˜155° C.

4-[2-(4-Methylphenylthio)ethyl]aminoquinazoline

m.p. 134°˜136° C.

2-Chloro-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 161°˜163° C.

2-Chloro-4-[2-(4-methylphenylthio)ethyl]aminoquinazoline

m.p. 160°˜165° C.

6-Methyl-4-[2-(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 143°˜145° C.

4-[2-(4-tert-Butylphenoxy)ethyl]aminoquinazoline

m.p. 138°˜143° C.

4-[2-(4-Methoxyphenoxy)ethyl]aminoquinazoline

m.p. 142°˜144° C.

4-[2-(2,4-Dichlorophenoxy)ethyl]aminoquinazoline

m.p. 170°˜172° C.

4-[2-(2,4-Dibromophenoxy)ethyl]aminoquinazoline

m.p. 161°˜163° C.

6-Chloro-4-[2-(2,4-dichlorophenoxy)ethyl]aminoquinazoline

m.p. 187°˜188° C.

4-[2-(2-Methyl-4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 164°˜166° C.

2-Chloro-4-[2-(2-methyl-4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 179°˜181° C.

4-[2-(2,4-Dimethylphenoxy)ethyl]aminoquinazoline

m.p. 164°˜167° C.

4-[2-(2-Chloro-4-methoxyphenoxy)ethyl]aminoquinazoline

m.p. 124°˜126° C.

6-Chloro-4-[2-(2,5-dimethylphenoxy)ethyl]aminoquinazoline

m.p. 164°˜167° C.

4-[2-(2,6-Dimethylphenoxy)ethyl]aminoquinazoline

m.p. 132°˜134° C.

2-Chloro-4-[2-(2,6-dimethylphenoxy)ethyl]aminoquinazoline

m.p. 169°˜171° C.

4-[2-(3-Methyl-4-methylthiophenoxy)ethyl]aminoquinazoline

m.p. 171°˜173° C.

4-[2-(3,5-Dimethylphenoxy)ethyl]aminoquinazoline

m.p. 183°˜185° C.

2-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline

m.p. 186°˜188° C.

6-Chloro-4-[2-(3,5-dimethylphenoxy)ethyl]aminoquinazoline

m.p. 209°˜211° C.

4-[2-(2,4,5-Trichlorophenoxy)ethyl]aminoquinazoline

m.p. 176°˜178° C.

6-Chloro-4-[2-(2,4,5-trichlorophenoxy)ethyl]aminoquinazoline

m.p. 198°˜202° C.

4-[2-(2,4,6-Trichlorophenoxy)ethyl]aminoquinazoline

m.p. 170°˜172° C.

4-[2-(2,4,6-Triiodophenoxy)ethyl]aminoquinazoline

m.p. 185°˜187° C.

4-[2-(2,4,6-Tribromophenoxy)ethyl]aminoquinazoline

m.p. 181°˜183° C.

4-[2-(1-Naphthoxy)ethyl]aminoquinazoline

m.p. 163°˜165° C.

6-Chloro-4-[2-(1-naphthoxy)ethyl]aminoquinazoline

m.p. 165°˜167° C.

4-[2-Benzylthio)ethyl]aminoquinazoline

m.p. 111°˜113° C.

2-Chloro-4-[2-(benzylthio)ethyl]aminoquinazoline

m.p. 107°˜109° C.

4-(3-Methoxypropyl)aminoquinazoline

m.p. 105°˜107° C.

4-(3-Ethoxypropyl)aminoquinazoline

m.p. 101°˜103° C.

2-Chloro-4-(3-ethoxypropyl)aminoquinazoline

m.p. 92°˜95° C.

6-Nitro-4-(3-ethoxypropyl)aminoquinazoline

m.p. 141°˜143° C.

4-(3-Isopropoxypropyl)aminoquinazoline

m.p. 84°˜86° C.

4-(3-n-Butoxypropyl)aminoquinazoline

m.p. 77°˜79° C.

2-Chloro-4-(3-n-butoxypropyl)aminoquinazoline

m.p. 86°˜88° C.

4-[3-(2-Ethylhexyloxy)propyl]aminoquinazoline

m.p. 36°˜40° C.

6-Nitro-4-[3-(2-ethylhexyloxy)propyl]aminoquinazoline

m.p. 55°˜58° C.

4-(3-Phenylthiopropyl)aminoquinazoline

m.p. 103°˜105° C.

2-Chloro-4-(3-phenoxypropyl)aminoquinazoline

m.p. 118°˜120° C.

2-Chloro-4-(3-phenylthiopropyl)aminoquinazoline

m.p. 86°˜89° C.

6-Methyl-4-(3-phenoxypropyl)aminoquinazoline

m.p. 121°˜123° C.

6-Methyl-4-(3-phenylthiopropyl)aminoquinazoline

m.p. 121°˜123° C.

4-[3-(2-Chlorophenoxy)propyl]aminoquinazoline

m.p. 144°˜145° C.

4-[3-(2-Methylphenoxy)propyl]aminoquinazoline

m.p. 147°˜149° C.

4-[3-(2-Methylphenylthio)propyl]aminoquinazoline

m.p. 99°˜102° C.

4-[3-(2-Methoxyphenoxy)propyl]aminoquinazoline

m.p. 138°˜139° C.

4-[3-(3-Chlorophenoxy)propyl]aminoquinazoline

m.p. 145°˜147° C.

4-[3-(3-Methylphenoxy)propyl]aminoquinazoline

m.p. 153°˜155° C.

4-[3-(3-Methylphenylthio)propyl]aminoquinazoline

m.p. 73°˜76° C.

2-Chloro-4-[3-(3-methylphenoxy)propyl]aminoquinazoline

m.p. 96°˜99° C.

2-Chloro-4-[3-(3-methylphenylthio)propyl]aminoquinazoline

m.p. 70°˜73° C.

4-[3-(4-Chlorophenoxy)propyl]aminoquinazoline

m.p. 148°˜150° C.

2-Chloro-4-[3-(4-chlorophenoxy)propyl]aminoquinazoline

m.p. 131°˜133° C.

4-[3-(4-Methylphenoxy)propyl]aminoquinazoline

m.p. 151°˜152° C.

4-[3-(4-Methylphenylthio)propyl]aminoquinazoline

m.p. 129°˜131° C.

2-Chloro-4-[3-(4-methylphenylthio)propyl]aminoquinazoline

m.p. 82°˜85° C.

4-[3-(4-Methoxyphenoxy)propyl]aminoquinazoline

m.p. 136°˜138° C.

4-[3-(2,5-Dimethylphenoxy)propyl]aminoquinazoline

m.p. 142°˜144° C.

4-[3-(2-Methyl-4-chlorophenoxy)propyl]aminoquinazoline

m.p. 178°˜181° C.

4-[3-(2-Chloro-4-methoxyphenoxy)propyl]aminoquinazoline

m.p. 166°˜169° C.

4-[3-(3-Methyl-4-chlorophenoxy)propyl]aminoquinazoline

m.p. 137°˜139° C.

4-[3-(3,5-Dimethylphenoxy)propyl]aminoquinazoline

m.p. 116°˜118° C.

4-[3-(1-Naphthoxy)propyl]aminoquinazoline

m.p. 132°˜134° C.

4-(1-Methyl-2-phenoxyethyl)aminoquinazoline

m.p. 125°˜128° C.

2-Chloro-4-(1-methyl-2-phenoxyethyl)aminoquinazoline

m.p. 168°˜170° C.

6-Methyl-4-(1-methyl-2-phenoxyethyl)aminoquinazoline

m.p. 150°˜152° C.

4-[1-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 134°˜136° C.

4-[1-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline

m.p. 165°˜167° C.

4-[1-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline

m.p. 163°˜166° C.

4-[1-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

m.p. 130°˜132° C.

4-[1-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 156°˜159° C.

2-Chloro-4-[1-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 125°˜128° C.

4-[1-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 171°˜173° C.

2-Chloro-4-[1-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 139°˜141° C.

4-(2-Methyl-2-phenoxyethyl)aminoquinazoline

m.p. 162°˜164° C.

2-Chloro-4-(2-methyl-2-phenoxyethyl)aminoquinazoline

m.p. 144°˜146° C.

4-[2-Methyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline

m.p. 151°˜153° C.

4-[2-Methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 152°˜154° C.

2-Chloro-4-[2-methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 122°˜125° C.

4-[2-Methyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline

m.p. 135°˜138° C.

4-[2-Methyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline

m.p. 140°˜142° C.

4-[2-Methyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

m.p. 123°˜126° C.

4-[2-Methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 165°˜168° C.

2-Chloro-4-[2-methyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 160°˜162° C.

4-[2-Methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 163°˜164° C.

2-Chloro-4-[2-methyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 138°˜141° C.

4-(4-Phenoxybutyl)aminoquinazoline.monohydrate

m.p. 90°˜93° C.

6-Methyl-4-(4-phenoxybutyl)aminoquinazoline

m.p. 110°˜112° C.

4-[4-(2-Chlorophenoxy)butyl]aminoquinazoline

m.p. 151°˜153° C.

4-[4-(2-Methylphenoxy)butyl]aminoquinazoline

m.p. 152°˜153° C.

4-[4-(2-Methoxyphenoxy)butyl]aminoquinazoline

m.p. 135°˜137° C.

4-[4-(3-Methylphenoxy)butyl]aminoquinazoline

m.p. 110°˜112° C.

4-[4-(4-Methylphenoxy)butyl]aminoquinazoline

m.p. 121°˜123° C.

4-(2-Ethyl-2-phenoxyethyl)aminoquinazoline

m.p. 158°˜160° C.

4-(2,2-Dimethyl-2-phenoxyethyl)aminoquinazoline

m.p. 98°˜100° C.

2-Chloro-4-(2,2-dimethyl-2-phenoxyethyl)aminoquinazoline

m.p. 132°˜134° C.

4-[2,2-Dimethyl-2-(2-chlorophenoxy)ethyl]aminoquinazoline

m.p. 89°˜91° C.

4-[2,2-Dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 96°˜99° C.

2-Chloro-4-[2,2-dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline

m.p. 110°˜112° C.

4-[2,2-Dimethyl-2-(2-methoxyphenoxy)ethyl]aminoquinazoline

m.p. 103˜105° C.

4-[2,2-Dimethyl-2-(3-chlorophenoxy)ethyl]aminoquinazoline

m.p. 111°˜113° C.

4-[2,2-Dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

m.p. 97°˜100° C.

2-Chloro-4-[2,2-dimethyl-2-(3-methylphenoxy)ethyl]aminoquinazoline

m.p. 103°˜106° C.

4-[2,2-Dimethyl-2-(4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 104°˜106° C.

4-[2,2-Dimethyl-2-(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 92°˜94° C.

4-[5-(2-Chlorophenoxy)pentyl]aminoquinazoline

m.p. 115°˜117° C.

4-[5-(2-Methylphenoxy)pentyl]aminoquinazoline

m.p. 96°˜98° C.

4-[5-(2-Methoxyphenoxy)pentyl]aminoquinazoline

m.p. 104°˜106° C.

4-[5-(3-Methylphenoxy)pentyl]aminoquinazoline

m.p. 113°˜115° C.

4-[5-(4-Methylphenoxy)pentyl]aminoquinazoline

m.p. 128°˜130° C.

4-(6-Phenoxyhexyl)aminoquinazoline

m.p. 105°˜108° C.

4-(7-Phenoxyheptyl)aminoquinazoline

m.p. 83°˜86° C.

4-(8-Phenoxyoctyl)aminoquinazoline

m.p. 74°˜78° C.

4-[2-(2-n-Propylphenoxy)ethyl]aminoquinazoline

m.p. 74°˜78° C.

6-Methyl-4-[4-(2-chlorophenoxy)butyl]aminoquinazoline

m.p. 113°˜116° C.

4-[2-(2-Methoxy-4-methylphenoxy)ethyl]aminoquinazoline

m.p. 155°˜156° C.

4-[2-(3-Methoxyphenoxy)ethyl]aminoquinazoline

m.p. 165°˜166° C.

4-[2-(2-Methoxy-4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 163°˜166° C.

4-[2-(2-Methyl-3-chlorophenoxy)ethyl]aminoquinazoline

m.p. 154°˜156° C.

2-Methyl-4-(3-phenoxypropyl)aminoquinazoline

m.p. 111°˜115° C.

4-[2-(2,5-Dimethoxyphenoxy)ethyl]aminoquinazoline

m.p. 178°˜180° C.

4-[2-(3,5-Dimethyl-4-bromophenoxy)ethyl]aminoquinazoline

m.p. 218°˜220° C.

4-[2-(2,4-Dichloro-6-methylphenoxy)ethyl]aminoquinazoline

m.p. 165°˜167° C.

4-[2-(2-Trifluoromethyl-4-chlorophenoxy)ethyl]aminoquinazoline

m.p. 159°˜162° C.

6-Chloro-4-[2-(2-Chlorophenoxy)ethyl]aminoquinazoline

m.p. 176°˜178° C.

4-[2-(2-n-Butoxyphenoxy)ethyl]aminoquinazoline

m.p. 89°˜92° C.

4-[2-(2-Trifluoromethylphenoxy)ethyl]aminoquinazoline

m.p. 143°˜145° C.

4-[2-(4-Bromophenylthio)ethyl]aminoquinazoline

m.p. 162°˜163° C.

4-[2-(4-Isopropoxyphenoxy)ethyl]aminoquinazoline

m.p. 148°˜151° C.

4-[2-(2,4-Dibromophenoxy)ethyl]aminoquinazoline

m.p. 161°˜163° C.

6-Chloro-4-[2-(2,4,6-trichlorophenoxy)ethyl]aminoquinazoline

m.p. 185°˜187° C.

4-[2-(2,3,6-Trimethylphenoxy)ethyl]aminoquinazoline

m.p. 155°˜158° C.

4-[2-(Benzyloxy)ethyl]aminoquinazoline

m.p. 111°˜113° C.

4-(3-Phenoxypropyl)aminoquinazoline

m.p. 129°˜131° C.

6-Nitro-4-(3-phenoxypropyl)aminoquinazoline

m.p. 121°˜123° C.

2-Chloro-4-[3-(4-chlorophenoxy)propyl]aminoquinazoline

m.p. 131°˜133° C.

2-Chloro-4-[2,2-dimethyl-2(4-methylphenoxy)ethyl]aminoquinazoline

m.p. 121°˜124° C.

4-(5-Phenoxypentyl)aminoquinazoline

m.p. 106°˜108° C.

4-[6-(2-Methylphenoxy)hexyl]aminoquinazoline

m.p. 90°˜92° C.

4-[7-(2-Methylphenoxy)heptyl]aminoquinazoline

m.p. 88°˜91° C.

4-[8-(2-Methylphenoxy)octyl]aminoquinazoline

m.p. 70°˜73° C.

4-[12-(2-Methylphenoxy)dodecyl]aminoquinazoline

m.p. 66°˜70° C.

4-[2-(2-n-Butylphenoxy)ethyl]aminoquinazoline

m.p. 159°˜163° C.

4-[2-(2-tert-Butylphenoxy)ethyl]aminoquinazoline

m.p. 158°˜160° C.

The compounds in this invention may be formulated for use with thepreparations commonly employed as an agricultural fungicide, forexample, powdery dusts, coarse dusts, fine granules, granules, wettablepowders, emulsifiable concentrates, aqueous liquids, water solublepowders, oil suspensions and so on, with admixture of a carrier and, ifrequired, other auxiliary agents. The carrier as used herein means asynthetic or natural and inorganic or organic substance that is mixedwith an active compound and can assist an active compound in its arrivalto the sitis to be treated and make it easy to store, transport orhandle.

As suitable solid carriers may be mentioned inorganic substances such asclays, which may be represented by Kaolinite, Montmorillonite orAttapulgite, talc, mica, pyrophyllite, pumice, vermiculite, gypsum,calcium carbonate, dolomite, diatomaceous earth, magnesium carbonate,apatite, zeolite, silicic anhydride, synthetic calcium silicate and thelike, vegetable organic substances such as soybean meal, tobacco powder,walnut powder, wheat flour, wood meal, starch, crystalline cellulose andthe like, synthetic or natural high polymer compounds such as cumaroneresin, petroleum resin, alkyd resin, polyvinyl chloride, polyalkyleneglycol, ketone resin, ester gum, copal gum, dammar gum, and the like,waxes such as carnauba wax, beeswax and the like, or urea.

As suitable liquid media or carriers may be mentioned paraffin ornaphthene hydrocarbons such as kerosine, mineral oil, spindle oil, whiteoil and the like, aromatic hydrocarbons such as benzene, toluene,xylene, ethylbenzene, cumene, methylnaphthalene and the like,chlorinated hydrocarbons such as carbon tetra chloride, chloroform,trichloroethylene, monochlorobenzene, o-chlorotoluene and the like,ethers such as dioxane, tetrahydrofuran and the like, ketones such asacetone, methyl ethyl ketone, diisobutylketone, cyclohexanone,acetophenone, isophorone and the like, esters such as ethyl acetate,amyl acetate, ethylene glycol acetate, diethylene glycol acetate,dibutyl maleate, diethyl succinate and the like, alcohols such asmethanol, n-hexanol, ethylene glycol, diethylene glycol, cyclohexanol,benzyl alcohol and the like, ether alcohols such as ethylene glycolethyl ether, ethylene glycol phenyl ether, diethylene glycol ethylether, diethylene glycol butyl ether and the like, polar solvents suchas dimethylformamide, dimethylsulfoxide and the like, or water.

As the surface active agents used for emulsifying, dispersing, wetting,spreading, binding, controlling disintegration, stabilizing activeingredient, improving fluidity, rust proofing and so on may be utilizedany of non-ionic, anionic, cationic and amphoteric ones, but non-ionicand/or anionic agents are usually employed. As suitable non-ionicsurface active agents may be mentioned, for example, polymerizationadducts of ethylene oxide and higher alcohols such as lauryl alcohol,stearyl alcohol, oleyl alcohol and the like, polymerization adducts ofethylene oxide and alkyl phenols such as isooctyl phenol, nonyl phenoland the like, polymerization adducts of ethylene oxide and alkylnaphthols such as butyl naphthol, octyl naphthol and the like,polymerization adducts of ethylene oxide and higher fatty acids such aspalmitic acid, stearic acid, oleic acid and the like, polymerizationadducts of ethylene oxide and mono- or di-alkyl phosphoric acids such asstearyl phosphoric acid, dilauryl phosphoric acid and the like,polymerization adducts of ethylene oxide and amines such as dodecylamine, stearic acid amide and the like, polymerization adducts ofethylene oxide and higher fatty acid esters of polyhydric alcohols suchas sorbitan and said fatty acid esters, polymerization adducts ofethylene oxide of propylene oxide and so on. As suitable anionic surfaceactive agents may be mentioned, for example, alkyl sulfate salts such assodium lauryl sulfate, oleyl sulfate amine salt and the like, alkylsulfonate salts such as sodium dioctyl sulfosuccinate, sodium2-ethylhexene sulfonate and the like, aryl sulfonate salts such assodium isopropylnaphthalene sulfonate, sodium methylenebisnaphthalenesulfonate, sodium ligninsulfonate, sodium dodecylbenzene sulfonate andthe like.

Moreover, the agricultural fungicidal compositions of this invention maybe used in combination with high molecular compounds or other auxiliaryagents such as casein, gelatin, albumin, glue, sodium alginate,carboxymethyl cellulose, methyl cellulose, hydroxyethyl cellulose,polyvinyl alcohol and the like for improving properties and increasingbiological effects thereof.

The above-mentioned carriers and various auxiliary agents may beoptionally utilized alone or in combination for desired purposes, withconsideration for the type of preparation, application and otherfactors.

Dusts usually contain, for example, 1 to 25 parts by weight of theactive compound and the remainder is a solid carrier.

Wettable powders usually contain, for example, 25-90 parts by weight ofthe active compound and the remainder is a solid carrier and adispersing and wetting agent, if required, together with a protectivecolloidal agent, a thixotropic agent, an anti-foaming agent and thelike.

Granules usually contain 1-35 parts by weight of the active compound anda major portion of the remainder is a solid carrier. The active compoundis homogeneously admixed with the solid carrier or adhered or adsorbedon the carrier surface and the size of a granule is about 0.2-1.5 mm.

Emulsifiable concentrates usually contain, for example, 5-50 parts byweight of the active compound and about 5-20 parts by weight of anemulsifying agent, the remainder being a liquid carrier, if required,together with a corrosive inhibitor.

The fungicidal compositions of this invention which are formulated intovarious types of preparations as above, may be applied in a paddy orupland field at 1-5000 g, preferably 10-1000 g of the active ingredientper 10 acres, for pre- or post-emergence foliage spraying or soildrenching or spraying onto water to control diseases effectively.

Further, the fungicidal compositions of this invention, when employedfor seed disinfection or coating, may effectively control soil-borne orseed infectious diseases by coating seeds at 0.1-2%, preferably0.2-0.5%, of the active ingredient per weight of the seed.

The fungicidal compositions of this invention may be preferably combinedwith other fungicides for broader fungicidal spectra and, in some cases,a synergistic effect is expectable.

As examples of such other fungicides may be, for instance, carbamatetype fungicides such as3,3'-ethylene-bis(tetrahydro-4,6-dimethyl-2H-1,3,5-thiadiazine-2-thione;zinc or manganese ethylenebisdithiocarbamate;bis(dimethyldithiocarbamoyl)disulfide; zinc propylenebisdithiocarbamate;bis(dimethyldithiocarbamoyl)ethylenediamine; nickeldimethyldithiocarbamate; methyl1-(butylcarbamoyl))-2-benzimidazolcarbamate;1,2-bis(3-methoxycarbonyl-2-thioureido)benzene; phosphorous typefungicides such as O,O-diisopropyl-S-benzylphosphorothioate;O-ethyl-S,S-diphenyldithiophosphate and the like, dicarboximide typefungicides such asN-trichloromethylthio-4-cyclohexene-1,2-dicarboximide;N-tetrachloroethylthio-4-cyclohexene-1,2-dicarboximide and the like,oxazine type fungicides such as5,6-dihydro-2-methyl-1,4-oxazine-3-carboxanilide-4,4-dioxide;5,6-dihydro-2-methyl-1,4-oxazine-3-carboxanilide and the like,naphthoquinone type fungicides such as 2,3-dichloro-1,4-naphthoquinoneand the like, other fungicides such as pentachloronitrobenzene;3-hydroxy-5-methylisoxazole; N-(2,3-dichlorophenyl)tetrachlorophthalamicacid; 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole;2,4,6-trichloro-6-(o-chloroanilino)-1,3,5-triazine;2,3-dicyano-1,4-dithioanthraquinone; copper 8-quinolate; Validamycin;cycloheximide; iron methanearsonate; tetrachloroisophthalonitrile;2-(1-methylpropyl)-4,6-dinitrophenyl β,β-dimethylacrylate;triphenyltinhydroxide; Polyoxin; Phytomycin, Kasugamycin; Blasticidin S;4,5,6,7-tetrachlorophthalide and the like, but they are not critical.

The fungicidal compositions of the invention may also be applied in amixture with insecticides as illustratively given below: phosphorus typeinsecticides such as O,O-diethylO-(2-isopropyl-4-methyl-6-pyrimidinyl)phosphorothioate; O,O-diethylS-2-[(ethylthio)ethyl]phosphorodithioate; O,O-dimethylO-(3-methyl-4-nitrophenyl)thiophosphate; O,O-dimethylS-(N-methylcarbamoylmethyl)phosphorodithioate; O,O-dimethylS-(N-methyl-N-formylcarbamoylmethyl)phosphorodithioate; O,O-dimethylS-2-(ethylthio)ethylphosphorodithioate;O,O-dimethyl-1-hydroxy-2,2,2-trichloroethylphosphonate;O,O-diethyl-O-(5-phenyl-3-isoxazolyl)-phosphorothioate;methyl(4-bromo-2,5-dichlorophenyl)-phenylphosphonothioate;O,O-dimethyl-O-(3-methyl-4-methylmercaptophenyl)thiophosphate;O-ethyl-O-p-cyanophenyl phenylphosphonothioate; O,O-diethylS-(1,2-dicarboethoxyethyl)phosphorodithioate;2-chloro-1-(2,4,5-trichlorophenyl) vinyldimethyl phosphate;2-chloro-1-(2,4-dichlorophenyl)-vinyldimethyl phosphate; O,O-dimethylO-p-cyanophenyl phosphorothioate; 2,2-dichlorovinyl dimethyl phosphate;O,O-diethyl O-2,4-dichlorophenyl phosphorothioate; ethylmercaptophenylacetate O,O-dimethyl phosphorodithioate;S-[(6-chloro-2-oxo-3-benzoxazolinyl)-methyl]O,O-diethylphosphorodithioate;4-mercaptothiophenyl dipropylphosphate;2-chloro-1-(2,4-dichlorophenyl)vinyl diethylphosphate;O,O-diethyl-O-(3-oxo-2-phenyl-2H-pyridazin-6-yl)phosphorothioate;O,O-dimethyl S-(1-methyl-2-ethylsulfinyl)-ethyl phosphorothiolate;O,O-dimethyl S-phthalimidomethyl phosphoroditioate;dimethylmethylcarbamoylethylthioethyl thiophosphorothiolate; O,O-diethylS-(N-ethoxycarbonyl-N-methylcarbamoylmethyl) phosphorodithioate;O,O-dimethyl-S-[2-methoxy-1,3,4-thiadiazol-5(4H)-onyl-(4)-methyl]dithiophosphate;2-methoxy-4H-1,3,2-benzodioxaphosphorin 2-sulfide;O,O-diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate;O-ethyl-O-2,4-dichlorophenyl thionobenzene phosphonate;S-[4,6-diamino-S-triazin-2-yl-methyl]-O,O-dimethyl phosphorodithioate;O-ethyl O-p-nitrophenylphenylphosphorothioate; O,S-dimethyl-N-acetylphosphoroamidothioate or the like; carbamate type insecticides such as1-naphthyl N-methylcarbamate;S-methyl-N-[methylcarbamoyloxy]thioacetoimidate; m-tolylmethylcarbamate; 3,4-xylyl methylcarbamate; 3,5-xylyl methylcarbamate;2-sec-butylphenyl-N-methylcarbamate;2-isopropoxyphenyl-N-methylcarbamate;1,3-bis(carbamoylthio)-2-(N,N-dimethylamino)propane hydrochloride; andthe like, other insecticides such asN,N-dimethyl-N'-(2-methyl-4-chlorophenyl) formamidine hydrochloride,nicotine sulfate, Milbemycin, 6-methyl,2,3-quinoxalinedithiocyclicS,S-dithiocarbonate, 2,4-dinitro-6-sec-butylphenyl dimethylacrylate;1,1-bis(p-chlorophenyl)-2,2,2-trichloroethanol;2-(p-tert-butylphenoxy)isopropyl-2'-chloroethylsulfite; azoxybenzene;di-(p-chlorophenyl)-cyclopropyl carbinol;isopropyl-4,4'-dichlorobenzylate; ethyl-4,4'-dichlorobenzylate; ormachine oil and the like.

The fungicidal composition of this invention can be used with acontrolling agent against rice blast, Helminothosporium leaf spot,bacterial leaf blight, rice stem borer, planthopper and/or leafhopper tosave labor. The agricultural chemicals, which may be used with thepresent fungicidal composition, are as mentioned hereinabove. Thecombination ratio of these agents may vary depending upon diseases orinsects to be controlled and preparation forms to be used, these agentsare prepared and applied with an effective amount of active ingredientsrequired for controlling. In particular, dusts and fine granules arepreferable for controlling rice plant diseases and soil treatment.

Examples of the agricultural fungicidal composition of this inventionwill be given below. All parts are given by weight unless otherwisestated.

Formulation 1. Dusts

Five parts of the compound having compound No. 8, 50 parts of talc and45 parts of kaolin were uniformly mixed to form dusts.

Formulation 2. Wattable powders

Fifty parts of the compound having compound No. 20, 29 parts of clay, 10parts of diatomaceous earth, 5 parts of white carbon, 3 parts of sodiumlignosulfonate, 2 parts of "Newcol" 1106 (trade name, Nihon NyukazaiK.K. Japan) and 1 part of polyvinyl alcohol were uniformly mixed in amixer and pulverized three times by a hammer mill to give wettablepowders.

Formulation 3. Granules

Seventy parts of the compound having compound No. 32 was finelypulverized and 30 parts of clay was added thereto and then mixed in amixer to form a premixture. 10 parts of the premix was uniformly mixedwith 60 parts of clay and 30 parts of bentonite in a mixer. The mixturewas kneaded with a suitable amount of water in a kneader, extrudedthrough a screen having a diameter of 0.8 mm and dried in a draft drierat 50° C. The product thus formed was adjusted by a sifter to formgranules.

Experimental examples of the present fungicidal compositions thusprepared are given below. The wettable powders prepared according to theprocedures in the abovementioned Formulation 2 are used in the followingexperiments, each containing 50% by weight of the active compound ofthis invention.

Experiment 1 Test for Effect Against the Rice Blast

Rice plant seedlings, variety Nohrin No. 20, at 4 to 5 leaf stage weresprayed with each test preparation at 500 ppm in a total amount of 30 mlper 2 pots. After 3 days, the rice blast fungi were inoculated into thehost plants by spraying a spore suspension of Piricularia oryzae, andthe host plants were kept in a room for 48 hours under conditions at 20° to 22° C. 100% relative humidity. The host plants were then placed ina greenhouse at 24° to 26° C., and after further 3 days the number ofdiseased spots of the upper two leaves of the host plants wasinvestigated. Each test was conducted at triplicate runs and the damagewas indicated by the mean number of diseased spots per leaf.

The results are given in Table 1. None of the active compounds exhibitedphototoxicity.

                  Table 1.                                                        ______________________________________                                                   Number of               Number of                                             diseased                diseased                                   Test compound                                                                            spots per  Test compound                                                                              spots per                                  No.        leaf       No.          leaf                                       ______________________________________                                         4         0.0        110          1.0                                         6         0.9        111          1.0                                         9         1.0        112          0.9                                        13         0.1        121          0.7                                        20         1.1        122          1.2                                        21         0.8        135          0.9                                        42         1.0        137          0.1                                        52         1.1        141          1.4                                        55         0.9        142          1.1                                        57         1.2        144          1.3                                        68         0.0        159          0.0                                        93         1.0        160          0.8                                        94         1.1        173          0.0                                        96         1.3        179          1.2                                        98         1.0        204          1.1                                        102        1.1        222          1.2                                                              (hydro-                                                 103        0.9        chloride)                                               109        1.5                                                                ______________________________________                                    

Experiment 2 Test for Effect Against the Brown Spot of Rice Plants

Following the procedures of Experiment 1, but using a spore suspensionof Cochliobolus miyabeanus and test preparations at 500 ppm, the effectagainst the brown spot was tested. Each test was conducted at triplicateruns and the damage was indicated by the mean number of diseased spotsper leaf. The results are given in Table 2. None of the active compoundsexhibited any phytotoxicity.

                  Table 2.                                                        ______________________________________                                                         Number of diseased spots                                     Test compound No.                                                                              per leaf                                                     ______________________________________                                         2               0.0                                                           4               2.0                                                           6               0.0                                                          135              0.0                                                          222              3.2                                                          (hydrochloride)                                                               ______________________________________                                    

Experiment 3 Test for Effect Against the Bacterial Leaf Blight of RicePlants

Groups of rice plants, variety Kimmaze, were planted in a series ofWager pots having a surface area of 1/5000 are and grown to the flagleaf stage. Each rice plant was inoculated with a suspension ofpathogenic microorganism Xanthomonas oryzae by spraying and then keptfor 1 day in a room at 26° to 28° C., 100% relative humidity. The potswere placed in a greenhouse at 28° C. Three days after the inoculation,each pot was treated with 20 ml of an aqueous suspension containing 1000ppm of one of the active compounds shown in Table 3, applied to the hostplants by spraying over their stems and leaves. 20 days after theapplication of the active compounds, the diseased area percentage of theflag and second leaves was measured. Three pots were used for each test.The results are given in Table 3. Compounds No. 43 and No. 55 showedslight phytotoxicity.

                  Table 3.                                                        ______________________________________                                        Test compound                                                                            Diseased area                                                                            Test compound                                                                             Diseased area                               No.        (%)        No.         (%)                                         ______________________________________                                         3         17          95         14                                          10         15         102         18                                          11         5          106         0                                           12         21         107         0                                           13         9          109         13                                          18         10         111         7                                           20         8          121         3                                           24         12         136         0                                           40         0          139         6                                           42         10         140         11                                          43         14         147         7                                           52         6          153         13                                          54         9          162         0                                           55         15         171         4                                           57         9          172         7                                           65         10         173         16                                          79         20         175         8                                           84         15         179         5                                           87         12         204         14                                          88         0          206         11                                          93         9          285         10                                          ______________________________________                                    

Experiment 4 Test for Effect Against the Late Blight of Tomatoes

Groups of tomatoes, variety Shinfukuju, at the 5 to 6 leaf stage weresprayed with 20 ml per pot of an aqueous suspension containing 500 ppmof one of the active compounds shown in Table 4. After air-drying, eachplant was inoculated with a spore suspension of pathogenic microorganismPhytophthora infestans by spraying and kept for 24 hours in a wet roomat 20° C. and more than 95% humidity. The pots were then kept in agreenhouse at 25° C., and after 5 days, the diseased area of the upperthree leaves of each plant was measured. Two pots were used for eachtest and the average diseased area per leaf was calculated. The resultsare given in Table 4. None of the active compounds exhibited anyphytotoxicity.

                  Table 4.                                                        ______________________________________                                                 Dis-              Dis-          Dis-                                 Test     eased   Test      eased Test    eased                                compound area    compound  area  compound                                                                              area                                 No.      (%)     No.       (%)   No.     (%)                                  ______________________________________                                         3       15      102       0     172     2                                     4       0       103       0     173     0                                     8       9       105       28    174     0                                     9       10      106       0     175     0                                    10       26                                                                   13       0                                                                    14       11      107       0     179     16                                   20       2       109       0     195     0                                    21       16      110       0     197     1                                    22       15      111       0     198     0                                    23       15      112       0     199     0                                    24       0       113       0     200     0                                    27       3       114       2     201     0                                    28       4       115       0     202     2                                    30       2       117       0     204     0                                    31       0       118       0     206     2                                    33       15      121       0     222     0                                    34       34      122       4     223     16                                   37       17      124       0     225     7                                    40       0       125       7     226     13                                   41       5       126       0     229     3                                    42       20      127       4     232     5                                    43       24      128       0     235     0                                    46       1       129       0     248     1                                    48       0       137       18    261     0                                    51       0       139       4     285     8                                    55       9       140       18    286     12                                   56       16      141       22    287     4                                    57       27      142       23    291     10                                   59       0       144       11    292     9                                    62       0       151       28    294     16                                   64       5       152       13    295     5                                    65       3       153       16                                                 73       3       154       5                                                  76       23      155       0                                                  79       21      157       0                                                  84       0       158       15                                                 87       0       159       0                                                                   164       27                                                                  170       0                                                  ______________________________________                                    

Experiment 5 Test for Effect Against the Early Blight of Tomatoes

Groups of two tomato plants, variety Shinfukuju, were planted in aseries of Wager pots having a diameter of 12 cm and used as host plantswhen at the 5 to 6 leaf stage. Each pot was treated with 30 ml of anaqueous suspension containing 500 ppm of one of the active compoundsshown in Table 5, applied to the host plants by spraying over theirstems and leaves. After air-drying, each plant was inoculated with aspore suspension of the pathogenic microorganism Alternalia solani andkept in a wet room for 24 hours at 20°-22° C., 100% relative humidity.The pots were then placed in a greenhouse for 3 days. The presence ofthe disease of all leaves was investigated and the number of diseasespots per leaf was calculated, using three pots for each test. Theresults are given in Table 5. None of the active compounds exhibited anyphytotoxicity.

                  Table 5.                                                        ______________________________________                                        Test       Number of  Test       Number of                                    compound   diseased spots                                                                           compound   diseased spots                               No.        per leaf   No.        per leaf                                     ______________________________________                                        6          16         125        3                                            14         0          127        6                                            20         0          131        7                                            21         37         142        25                                           30         5          144        20                                           32         25         151        19                                           39         9          152        3                                            42         10         153        2                                            47         0          157        0                                            49         0          158        14                                           53         20         159        0                                            55         32         160        0                                            65         2          170        16                                           68         0          172        0                                            71         6          173        20                                           73         12         175        0                                            87         25         177        0                                            94         49         183        4                                            96         13         195        0                                            97         0          197        14                                           98         0          198        0                                            102        0          200        27                                           103        29         202        10                                           104        0          204        0                                            106        14         206        0                                            109        18         222                                                     110        0          (hydro-    0                                                                  chloride)                                               111        7          223        10                                           113        6          225        18                                           117        12         232        9                                            118        34         235        0                                            120        27         285        7                                            122        16         286        7                                            124        23         287        7                                                                  291        3                                                                  295        7                                            ______________________________________                                    

Experiment 6 Test for Effect Against the Anthracnose of Cucumbers

Groups of two cucumber plants, variety Sagamihanshiro, were planted in aseries of Wagner pots having a diameter of 12 cm and used as host plantswhen the first leaf was fully grown and open. Each test group of threepots was treated with one of the active compounds shown in Table 6, byspraying on an aqueous suspension containing 500 ppm of the activecompound at the rate of 30 ml per 3 pots. After air-drying, the hostplants were inoculated by spraying with a spore suspension of thepathogenic microorganism Colletotrichum lagenarium and kept in a wetroom for 24 hours at 20° to 22° C., 100% relative humidity. The potswere then placed in a greenhouse at 26° C., and seven days after theinoculation, the diseased area percentage of the cotyledon and the firstleaf was calculated. The results are given in Table 6.

None of the active compounds exhibited any phytotoxicity.

                  Table 6.                                                        ______________________________________                                                  Dis-             Dis-          Dis-                                 Test     eased   Test      eased Test    eased                                compound area    compound  area  compound                                                                              area                                 No.      (%)     No.       (%)   No.     (%)                                  ______________________________________                                         2       14      103       0     158     16                                    4       6       106       0     159     0                                     6       0       107       0     170     0                                     8       0       109       0     172     0                                    13       0       110       0     173     0                                    20       5       112       3     174     0                                    23       0       113       0     175     21                                   28       2       114       0     179     2                                    30       0                                                                    35       0       117       5     197     0                                    39       11      118       0     200     2                                    41       0       119       13    201     0                                    42       20      122       0     204     1                                    46       5       124       0     222     0                                    47       13      125       0     223     3                                    48       0       126       0     225     10                                   51       0       127       4     226     0                                    55       8       128       6     229     5                                    57       17      129       0     232     31                                   59       12      136       19    234     0                                    62       0       137       0     248     12                                   65       0       141       0     261     7                                    68       0       142       15    285     11                                   70       0       144       0     286     2                                    79       0       147       12    287     0                                    84       12      152       9     288     2                                    85       8       153       9     290     0                                    102      0       155       6     291     0                                                                     295     2                                    ______________________________________                                    

Experiment 7 Test for Effect Against the Powdery Mildew of Cucumbers

Cucumber seedlings, variety Sagamihanshiro, planted two per 12 cmdiameter pot, were used as host plants at the stage when the first leafwas fully grown and open. Each test group of three pots was treated withone of the active compounds shown in Table 7, by spraying on an aqueoussuspension containing 500 ppm of the active compound at the rate of 20ml per 3 pots. After air-drying, the host plants were inoculated withSphaerotheca fuliginea by brushing already infected cucumber leaves witha small brush and letting the microorganism fall onto the host plants.The inoculated plants were kept in a greenhouse at 24° to 26° C. for 10days, and at the end of this period the diseased area percentage wasmeasured. Three pots were used for each test. The results are given inTable 7. None of the active compounds exhibited any phytotoxicity.

                  Table 7.                                                        ______________________________________                                                 Dis-              Dis-          Dis-                                 Test     eased   Test      eased Test    eased                                compound area    compound  area  compound                                                                              area                                 No.      (%)     No.       (%)   No.     (%)                                  ______________________________________                                         6       18       70       5     147     8                                     8       0        71       13    154     8                                    13       0        79       2     163     13                                   14       3        84       0     170     7                                    20       0        85       0     171     10                                   23       7       102       5     173     0                                    24       30      103       19    174     0                                    27       0       106       0     175     15                                   28       2       107       0     179     3                                    30       0       110       8     195     4                                    31       0       111       13    197     3                                    35       0       113       4     204     7                                    37       3       114       0     206     0                                    39       6       118       28    222                                                                           (hydro- 0                                    40       9       120       20    chloride)                                    41       0       124       4     225     0                                    43       0       126       18    226     3                                    46       0       127       8     232     0                                    47       11      128       18    234     0                                    55       2                                                                    56       4                                                                    57       17      129       7     248     8                                    59       23      135       0     261     5                                    62       0       137       0     286     0                                    64       10      142       10    287     10                                   65       0       142       12    288     6                                    67       5       144       12    290     3                                                                     295     3                                    ______________________________________                                    

Experiment 8 Test for Repellent Action Against the Fourth Instar Larvaof Cabbage Armyworms

Cabbage leaves were dipped for 30 seconds in an aqueous suspensioncontaining 1000 ppm or 100 ppm of one of the active compounds shown inTable 8. After air-drying, the leaves were placed on vermiculite in aplastic receptacle of 15 cm×20 cm, and five per receptacle of the fourthinstar larvae of cabbage armyworm were released on the leaves, whileother leaves without dipping being placed 12 cm away from the dippedleaves in the receptacle.

After 24 hours, the extent of ingestion of the dipped and non-dippedleaves was measured, using two receptacles for each test.

The results are given in Table 8.

                  Table 8.                                                        ______________________________________                                                  Extent of ingestion                                                 Test compound                                                                             1000 ppm       100 ppm                                            No.         Dipped  Non-dipped Dipped                                                                              Non-dipped                               ______________________________________                                         8          --      +++        ±  +++                                      41          --      +++        ±  +++                                      Control (None)      +++              +++                                      ______________________________________                                    

Experiment 9 Test for Repellent Action Against the Third Instar Larva ofTobacco Cutworm

Cabbage leaves were dipped for 30 seconds in an aqueous suspensioncontaining 1000 ppm or 100 ppm of one of the active compounds shown inTable 9. After air-drying, the leaves were placed in a plasticreceptacle having a diameter of 8 cm, and 10 per receptacle of the thirdinstar larvae of tobacco cutworm were released on the leaves. After 72hours, the extent of ingestion of the leaves was measured, using tworeceptacles for each test. The results are given in Table 9.

                  Table 9.                                                        ______________________________________                                        Test compound                                                                             Extent of ingestion                                               No.         1000 ppm       100 ppm                                            ______________________________________                                         62         --             --                                                 102         ±           +                                                  113         --             ±                                               118         ±           +                                                  126         --             ±                                               128         --             ±                                               Control (None)                                                                            +++            +++                                                ______________________________________                                    

What is claimed is:
 1. A method for protecting plants from fungicidalattack comprising applying to the site of said plants an agriculturalfungicidal composition which contains as an active ingredient afungicidally effective amount of a compound having the formula ##STR3##wherein: A and B are same or different and each represents a hydrogenatom, a lower alkyl group, a halogen atom or a nitro group;X representsan alkylene group; Y represents an oxygen atom or a sulfur atom; and Zrepresents an alkyl group, an aralkyl group, a naphthyl group, anunsubstituted phenyl group or a phenyl group substituted with 1 to 3substituents which are same or different and are selected from the groupconsisting of a lower alkyl group, a lower alkoxy group, a loweralkylthio group, a phenyl group, a trifluoromethyl group and a halogenatom; or a salt thereof;and an agriculturally acceptable carrier.
 2. Themethod of claim 1 wherein A and B are same or different and eachrepresents a hydrogen atom, a methyl group, a chlorine atom or a nitrogroup.
 3. The method of claim 1 wherein A is a hydrogen atom or achlorine atom and B is a hydrogen atom, methyl group, a chlorine atom ora nitro group.
 4. The method of claim 1 wherein both A and B arehydrogen atoms.
 5. The method of claim 1 wherein X is a straight orbranched chain alkylene group having 2 to 8 carbon atoms.
 6. The methodof claim 1 wherein Z is a straight or branched chain alkyl group having1 to 8 carbon atoms, a benzyl group, a naphthyl group, an unsubstitutedphenyl group or a phenyl group substituted with 1 to 3 substituentswhich are same or different and are selected from an alkyl having 1 to 4carbon atoms, an alkoxy having 1 to 4 carbon atoms, an alkylthio having1 to 4 carbon atoms, a phenyl, a trifluoromethyl and a halogen.
 7. Themethod of claim 1 wherein Z is an unsubstituted phenyl group or a phenylgroup substituted with 1 to 3 substituents which are same or differentand are selected from the group consisting of a methyl, methoxy, ethoxy,methylthio, trifluoromethyl and chlorine.
 8. The method of claim 1wherein Z is an unsubstituted phenyl group or a phenyl group substitutedwith a methyl, methoxy, ethoxy or chlorine.
 9. The method of claim 1wherein A is a hydrogen atom or a chlorine atom, B is a hydrogen atom, amethyl group, a chlorine atom or a nitro group, X is a straight orbranched chain alkylene group having 2 to 8 carbon atoms and Z is anunsubstituted phenyl group or a phenyl group substituted with 1 to 3substituents which are same or different and are selected from the groupconsisting of a methyl, methoxy, ethoxy, methylthio and chlorine. 10.The method of claim 1 wherein both A and B are hydrogen atoms, X is astraight or branched chain alkylene group having 2 to 8 carbon atoms andZ is an unsubstituted phenyl group or a phenyl group substituted with amethyl, methoxy, ethoxy or chlorine.
 11. The method of claim 1 whereinboth A and B are hydrogen atoms, X is a straight or branched chainalkylene group having 2 to 8 carbon atoms, Y is an oxygen atom and Z isan unsubstituted phenyl group or a phenyl group substituted with amethyl, methoxy, ethoxy or chlorine.
 12. The method of each of claims 1through 4, wherein X is a straight or branched chain alkylene grouphaving 2 to 8 carbon atoms.
 13. The method of claim 12, wherein Z is anunsubstituted phenyl group or a phenyl group substituted with a methyl,methoxy, ethoxy or chlorine.
 14. The method of claim 1 wherein saidactive ingredient is 4-[2-(2-chlorophenoxy)ethyl]aminoquinazoline. 15.The method of claim 1 wherein said active ingredient is4-[2-(2-methylphenoxy)ethyl]aminoquinazoline.
 16. The method of claim 1wherein said active ingredient is4-[2-(2-ethylphenoxy)ethyl]aminoquinazoline.
 17. The method of claim 1wherein said active ingredient is4-[2-(2-isopropylphenoxy)ethyl]aminoquinazoline.
 18. The method of claim1 wherein said active ingredient is4-[2-(2-sec-butylphenoxy)ethyl]aminoquinazoline.
 19. The method of claim1 wherein said active ingredient is4-[2-(2-trifluoromethylphenoxy)ethyl]aminoquinazoline.
 20. The method ofclaim 1 wherein said active ingredient is4-[2-(4-methylphenoxy)ethyl]aminoquinazoline.
 21. The method of claim 1wherein said active ingredient is4-[2-(2-methyl-4-chlorophenoxy)ethyl]aminoquinazoline.
 22. The method ofclaim 1 wherein said active ingredient is4-[2-(2,4-dimethylphenoxy)ethyl]aminoquinazoline.
 23. The method ofclaim 1 wherein said active ingredient is6-chloro-4-[2-(2,5-dimethylphenoxy)ethyl]aminoquinazoline.
 24. Themethod of claim 1 wherein said active ingredient is4-[3-(2-methylphenoxy)propyl]aminoquinazoline.
 25. The method of claim 1wherein said active ingredient is4-[2-methyl-2-(2-methylphenoxy)ethyl]aminoquinazoline.
 26. The method ofclaim 1 wherein said active ingredient is4-[4-(2-methylphenoxy)butyl]aminoquinazoline.
 27. The method of claim 1wherein said active ingredient is4-[1,1-dimethyl-2-(2-methylphenoxy)ethyl]aminoquinazoline.
 28. Themethod of claim 1 wherein said active ingredient is4-[5-(2-methylphenoxy)pentyl]aminoquinazoline.
 29. The method of claim 1wherein said active ingredient is4-[6-(2-methylphenoxy)hexyl]aminoquinazoline.
 30. The method of claim 1wherein said active ingredient is4-[7-(2-methylphenoxy)heptyl]aminoquinazoline.
 31. The method of claim 1wherein said active ingredient is4-[8-(2-methylphenoxy)octyl]aminoquinazoline.
 32. The method of claim 1wherein said active ingredient is4-[2-(2-n-propylphenoxy)ethyl]aminoquinazoline.
 33. The method of claim1 wherein said active ingredient is4-[2-(2-n-butylphenoxy)ethyl]aminoquinazoline.